I have the medium and just find at times when I have things other than my essentials I want something bigger.

Basically is the XL full on messenger size or does it lend to commuting/adding-your- shopping-list well?

Also I'm 5'8" and 145lbs, will I even be able to wear the XL?

You'll be able to fit inside the XL.

hahaha, true story.

YAY! Wait how do I bike home in my own bag?

Internet sarcasm... Are you saying XL is just unnecessarily big for me?

The XL is way bigger than anything I'd ever need. What type of stuff are you carrying?

Well all the tools and such for emergency, some extras in case I find something large I want and don't want to wait to buy, jacket, work clothes. That basically fills my medium now. I can get more in, but its pretty stuffed. and a pair of shoes for work

the XL is still 250ci smaller than Timbuk2's old Bolo bag from the late nineties, the problem with a bag that's too big is that you will carry too much stuff, just because you have space to hold it.

Get a large.

Thanks for the help

Scrod is right... unless you need to carry the kitchen sink, the L will do fine. You can haul a week's worth of groceries in it!

Heh, I'm only like 5'9"-10" and I have a Chrome Ivan. Thing. Is. Huge.

I do carry big things around to my friends house or whatever sometimes, so the space is nice.

I'd say if you want the extra space, get it! You'd probably be fine with the L though.

There's nothing wrong with an unusually large bag. I ride with a Chrome Kremlin all the time. It fits literally everything. Although I do occasionally get jokes about being a pizza delivery boy...

I have medium, large and XL Timbuk2 bags (they were super cheap on Chainlove a few years ago. Here are some photos of the only time I've had to carry enough stuff to use the XL. Check out the banana, the magazine, and the CD on the counter to give you an idea of the scale. I think there were 8 or 9 Priority Mail boxes in that bag. The XL can be overkill.